organic compounds
2-[(E)-({4-[(4,6-Dimethylpyrimidin-2-yl)sulfamoyl]phenyl}iminio)methyl]-6-hydroxyphenolate
aDepartment of Physics, University of Sargodha, Sargodha, Pakistan, bDepartment of Pharmacy Services, Jinnah Hospital, Lahore, Pakistan, cDepartment of Chemistry, Forman Christian College, Lahore 54600, Pakistan, dDepartment of Chemistry, Government Post Graduate College, Gojra, Punjab, Pakistan, and eDepartment of Chemistry, Bahauddin Zakariya University, Multan 60800, Pakistan
*Correspondence e-mail: dmntahir_uos@yahoo.com
The title compound, C19H18N4O4S, exists as a zwitterion in the solid state, with nominal proton transfer from a phenol group to the imine N atom. The 2,3-dihydroxybenzaldehyde fragment is oriented at a dihedral angle of 35.51 (11)° to the adajacent aniline group and makes a dihedral angle of 76.99 (6)° with the 4,6-dimethylpyrimidin-2-amine group. Intramolecular O—H⋯O and N—H⋯O hydrogen bonds close S(5) and S(6) rings, respectively; the same O atom accepts both bonds. In the crystal, polymeric chains along [001] are formed from molecules joined end-to-end by N—H⋯O and O—H⋯N hydrogen bonds; these feature R23(6) loops. The polymeric chains are linked by C—H⋯O interactions and there are π–π interactions between the pyrimidine rings with a centroid–centroid distance of 3.446 (2) Å.
Related literature
For related structures, see: Chohan et al. (2008); Shad et al. (2009); Tahir et al. (2012). For graph-set notation, see: Bernstein et al. (1995).
Experimental
Crystal data
|
Refinement
|
Data collection: APEX2 (Bruker, 2007); cell SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON.
Supporting information
10.1107/S1600536812034757/hb6908sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812034757/hb6908Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812034757/hb6908Isup3.cml
Equimolar quantities of 4-amino-N-(4,6-dimethylpyrimidin-2-yl) benzenesulfonamide (Sulfamethazine) and 2,3-dihydroxybenzaldehyde were refluxed in methanol along with few drops of acetic acid as catalyst for 3 h. The solution was kept at room temperature which afforded dark red plates after four days upon slow evaporation of the solvent.
The coordinates of H1 were refined. The H-atoms were positioned geometrically (C–H = 0.93–0.96 Å, N—H= 0.86 Å, O—H= 0.82 Å) and refined as riding with Uiso(H) = xUeq(C, N, O), where x = 1.5 for hydroxy & methyl and x = 1.2 for other H-atoms.
Data collection: APEX2 (Bruker, 2007); cell
SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).C19H18N4O4S | F(000) = 1664 |
Mr = 398.43 | Dx = 1.369 Mg m−3 |
Orthorhombic, Pbcn | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2n 2ab | Cell parameters from 1778 reflections |
a = 24.7506 (12) Å | θ = 1.7–26.0° |
b = 12.1689 (6) Å | µ = 0.20 mm−1 |
c = 12.8408 (5) Å | T = 296 K |
V = 3867.5 (3) Å3 | Plate, dark red |
Z = 8 | 0.34 × 0.28 × 0.15 mm |
Bruker Kappa APEXII CCD diffractometer | 3796 independent reflections |
Radiation source: fine-focus sealed tube | 1778 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.069 |
Detector resolution: 8.00 pixels mm-1 | θmax = 26.0°, θmin = 1.7° |
ω scans | h = −30→29 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −15→15 |
Tmin = 0.935, Tmax = 0.971 | l = −15→14 |
16627 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.151 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0534P)2 + 1.0105P] where P = (Fo2 + 2Fc2)/3 |
3796 reflections | (Δ/σ)max < 0.001 |
259 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
C19H18N4O4S | V = 3867.5 (3) Å3 |
Mr = 398.43 | Z = 8 |
Orthorhombic, Pbcn | Mo Kα radiation |
a = 24.7506 (12) Å | µ = 0.20 mm−1 |
b = 12.1689 (6) Å | T = 296 K |
c = 12.8408 (5) Å | 0.34 × 0.28 × 0.15 mm |
Bruker Kappa APEXII CCD diffractometer | 3796 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 1778 reflections with I > 2σ(I) |
Tmin = 0.935, Tmax = 0.971 | Rint = 0.069 |
16627 measured reflections |
R[F2 > 2σ(F2)] = 0.054 | 0 restraints |
wR(F2) = 0.151 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | Δρmax = 0.21 e Å−3 |
3796 reflections | Δρmin = −0.28 e Å−3 |
259 parameters |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.33210 (4) | 0.16234 (8) | 0.39452 (7) | 0.0639 (3) | |
O1 | 0.14274 (12) | 0.0303 (2) | −0.1123 (2) | 0.0874 (11) | |
O2 | 0.07789 (15) | −0.0466 (3) | −0.2721 (3) | 0.1110 (16) | |
O3 | 0.30024 (11) | 0.2317 (2) | 0.46012 (18) | 0.0765 (10) | |
O4 | 0.36264 (12) | 0.0762 (2) | 0.43976 (18) | 0.0799 (10) | |
N1 | 0.19699 (14) | −0.0123 (3) | 0.0534 (3) | 0.0683 (14) | |
N2 | 0.37120 (13) | 0.2493 (3) | 0.3342 (2) | 0.0719 (11) | |
N3 | 0.42863 (12) | 0.3128 (3) | 0.2071 (2) | 0.0638 (11) | |
N4 | 0.41470 (12) | 0.1191 (3) | 0.2320 (2) | 0.0650 (12) | |
C1 | 0.15104 (16) | −0.1524 (3) | −0.0429 (3) | 0.0673 (17) | |
C2 | 0.13077 (16) | −0.0756 (3) | −0.1170 (3) | 0.0683 (16) | |
C3 | 0.09721 (18) | −0.1143 (3) | −0.1978 (3) | 0.0783 (17) | |
C4 | 0.08434 (18) | −0.2239 (4) | −0.2017 (4) | 0.091 (2) | |
C5 | 0.10447 (18) | −0.2985 (3) | −0.1295 (4) | 0.0843 (19) | |
C6 | 0.13772 (17) | −0.2643 (3) | −0.0517 (3) | 0.0773 (17) | |
C7 | 0.18412 (16) | −0.1152 (3) | 0.0396 (3) | 0.0700 (17) | |
C8 | 0.22986 (15) | 0.0266 (3) | 0.1351 (3) | 0.0567 (14) | |
C9 | 0.27177 (16) | −0.0346 (3) | 0.1735 (3) | 0.0667 (16) | |
C10 | 0.30228 (15) | 0.0054 (3) | 0.2545 (3) | 0.0653 (14) | |
C11 | 0.29108 (14) | 0.1070 (3) | 0.2961 (2) | 0.0523 (12) | |
C12 | 0.24920 (16) | 0.1698 (3) | 0.2564 (3) | 0.0633 (14) | |
C13 | 0.21849 (16) | 0.1290 (3) | 0.1757 (3) | 0.0653 (14) | |
C14 | 0.40682 (15) | 0.2243 (3) | 0.2534 (3) | 0.0613 (16) | |
C15 | 0.46458 (16) | 0.2897 (3) | 0.1314 (3) | 0.0663 (16) | |
C16 | 0.47691 (16) | 0.1837 (3) | 0.1050 (3) | 0.0730 (16) | |
C17 | 0.45058 (16) | 0.0989 (3) | 0.1559 (3) | 0.0683 (16) | |
C18 | 0.45913 (17) | −0.0204 (3) | 0.1284 (3) | 0.0923 (19) | |
C19 | 0.48948 (18) | 0.3859 (3) | 0.0768 (3) | 0.0920 (19) | |
H1 | 0.1840 (16) | 0.024 (3) | 0.010 (3) | 0.0821* | |
H2 | 0.08717 | 0.01670 | −0.25928 | 0.1666* | |
H2A | 0.36975 | 0.31672 | 0.35398 | 0.0861* | |
H4 | 0.06153 | −0.24894 | −0.25413 | 0.1089* | |
H5 | 0.09512 | −0.37230 | −0.13437 | 0.1011* | |
H6 | 0.15163 | −0.31479 | −0.00446 | 0.0928* | |
H7 | 0.19743 | −0.16678 | 0.08640 | 0.0841* | |
H9 | 0.27959 | −0.10292 | 0.14484 | 0.0801* | |
H10 | 0.33052 | −0.03633 | 0.28130 | 0.0782* | |
H12 | 0.24188 | 0.23889 | 0.28391 | 0.0759* | |
H13 | 0.19016 | 0.17036 | 0.14875 | 0.0779* | |
H16 | 0.50251 | 0.16893 | 0.05389 | 0.0876* | |
H18A | 0.43576 | −0.04011 | 0.07173 | 0.1383* | |
H18B | 0.45100 | −0.06537 | 0.18778 | 0.1383* | |
H18C | 0.49606 | −0.03159 | 0.10819 | 0.1383* | |
H19A | 0.46303 | 0.42001 | 0.03270 | 0.1379* | |
H19B | 0.51940 | 0.36133 | 0.03535 | 0.1379* | |
H19C | 0.50198 | 0.43815 | 0.12743 | 0.1379* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0759 (7) | 0.0645 (6) | 0.0512 (5) | −0.0047 (6) | 0.0066 (5) | −0.0030 (5) |
O1 | 0.112 (2) | 0.0531 (16) | 0.097 (2) | 0.0023 (16) | −0.0265 (17) | −0.0057 (15) |
O2 | 0.141 (3) | 0.080 (2) | 0.112 (3) | 0.012 (2) | −0.051 (2) | −0.016 (2) |
O3 | 0.090 (2) | 0.0805 (18) | 0.0591 (15) | −0.0076 (15) | 0.0199 (14) | −0.0167 (14) |
O4 | 0.099 (2) | 0.0790 (18) | 0.0618 (16) | 0.0104 (16) | −0.0146 (15) | 0.0079 (14) |
N1 | 0.083 (3) | 0.060 (2) | 0.062 (2) | 0.0034 (19) | −0.0070 (19) | 0.0035 (18) |
N2 | 0.081 (2) | 0.0598 (18) | 0.075 (2) | −0.0124 (17) | 0.0241 (19) | −0.0180 (17) |
N3 | 0.066 (2) | 0.068 (2) | 0.0573 (19) | −0.0040 (17) | −0.0016 (16) | 0.0028 (16) |
N4 | 0.065 (2) | 0.068 (2) | 0.062 (2) | −0.0039 (17) | 0.0091 (17) | −0.0125 (17) |
C1 | 0.066 (3) | 0.062 (3) | 0.074 (3) | −0.001 (2) | 0.005 (2) | −0.007 (2) |
C2 | 0.071 (3) | 0.057 (2) | 0.077 (3) | −0.002 (2) | −0.001 (2) | −0.019 (2) |
C3 | 0.079 (3) | 0.070 (3) | 0.086 (3) | 0.003 (2) | −0.010 (3) | −0.015 (3) |
C4 | 0.090 (4) | 0.073 (3) | 0.109 (4) | −0.009 (3) | −0.010 (3) | −0.029 (3) |
C5 | 0.084 (3) | 0.059 (3) | 0.110 (4) | −0.011 (2) | 0.009 (3) | −0.017 (3) |
C6 | 0.080 (3) | 0.059 (3) | 0.093 (3) | −0.006 (2) | 0.016 (3) | 0.000 (2) |
C7 | 0.071 (3) | 0.062 (3) | 0.077 (3) | 0.003 (2) | 0.009 (2) | 0.005 (2) |
C8 | 0.068 (3) | 0.051 (2) | 0.051 (2) | −0.003 (2) | −0.0007 (19) | 0.0017 (19) |
C9 | 0.076 (3) | 0.051 (2) | 0.073 (3) | 0.009 (2) | −0.002 (2) | −0.004 (2) |
C10 | 0.072 (3) | 0.055 (2) | 0.069 (2) | 0.008 (2) | −0.007 (2) | −0.002 (2) |
C11 | 0.061 (2) | 0.047 (2) | 0.049 (2) | −0.0016 (18) | 0.0038 (17) | 0.0042 (17) |
C12 | 0.086 (3) | 0.048 (2) | 0.056 (2) | 0.006 (2) | 0.013 (2) | −0.002 (2) |
C13 | 0.076 (3) | 0.060 (2) | 0.060 (2) | 0.015 (2) | −0.001 (2) | 0.005 (2) |
C14 | 0.061 (3) | 0.066 (3) | 0.057 (2) | −0.008 (2) | 0.002 (2) | −0.008 (2) |
C15 | 0.061 (3) | 0.087 (3) | 0.051 (2) | −0.006 (2) | −0.004 (2) | 0.006 (2) |
C16 | 0.071 (3) | 0.091 (3) | 0.057 (2) | 0.001 (2) | 0.009 (2) | −0.004 (2) |
C17 | 0.068 (3) | 0.081 (3) | 0.056 (2) | 0.002 (2) | −0.002 (2) | −0.004 (2) |
C18 | 0.106 (4) | 0.088 (3) | 0.083 (3) | 0.011 (3) | 0.017 (3) | −0.018 (3) |
C19 | 0.095 (4) | 0.104 (3) | 0.077 (3) | −0.013 (3) | 0.018 (2) | 0.023 (3) |
S1—O3 | 1.430 (3) | C8—C13 | 1.380 (5) |
S1—O4 | 1.417 (3) | C9—C10 | 1.374 (5) |
S1—N2 | 1.630 (3) | C10—C11 | 1.375 (5) |
S1—C11 | 1.755 (3) | C11—C12 | 1.385 (5) |
O1—C2 | 1.324 (4) | C12—C13 | 1.378 (5) |
O2—C3 | 1.348 (5) | C15—C16 | 1.368 (5) |
O2—H2 | 0.8200 | C15—C19 | 1.497 (5) |
N1—C7 | 1.304 (5) | C16—C17 | 1.385 (5) |
N1—C8 | 1.409 (5) | C17—C18 | 1.509 (5) |
N2—C14 | 1.395 (5) | C4—H4 | 0.9300 |
N3—C15 | 1.347 (5) | C5—H5 | 0.9300 |
N3—C14 | 1.343 (5) | C6—H6 | 0.9300 |
N4—C14 | 1.324 (5) | C7—H7 | 0.9300 |
N4—C17 | 1.343 (5) | C9—H9 | 0.9300 |
N1—H1 | 0.78 (4) | C10—H10 | 0.9300 |
N2—H2A | 0.8600 | C12—H12 | 0.9300 |
C1—C2 | 1.425 (5) | C13—H13 | 0.9300 |
C1—C6 | 1.406 (5) | C16—H16 | 0.9300 |
C1—C7 | 1.413 (5) | C18—H18A | 0.9600 |
C2—C3 | 1.410 (6) | C18—H18B | 0.9600 |
C3—C4 | 1.372 (6) | C18—H18C | 0.9600 |
C4—C5 | 1.390 (7) | C19—H19A | 0.9600 |
C5—C6 | 1.360 (6) | C19—H19B | 0.9600 |
C8—C9 | 1.369 (5) | C19—H19C | 0.9600 |
O3—S1—O4 | 119.31 (15) | N3—C14—N4 | 128.6 (3) |
O3—S1—N2 | 102.96 (16) | N2—C14—N3 | 114.1 (3) |
O3—S1—C11 | 109.37 (16) | N3—C15—C19 | 116.5 (3) |
O4—S1—N2 | 111.00 (17) | C16—C15—C19 | 122.0 (4) |
O4—S1—C11 | 108.66 (17) | N3—C15—C16 | 121.5 (4) |
N2—S1—C11 | 104.50 (15) | C15—C16—C17 | 118.7 (4) |
C3—O2—H2 | 109.00 | N4—C17—C18 | 116.0 (3) |
C7—N1—C8 | 124.4 (4) | C16—C17—C18 | 122.7 (3) |
S1—N2—C14 | 126.0 (3) | N4—C17—C16 | 121.2 (3) |
C14—N3—C15 | 114.7 (3) | C3—C4—H4 | 119.00 |
C14—N4—C17 | 115.2 (3) | C5—C4—H4 | 119.00 |
C7—N1—H1 | 110 (3) | C4—C5—H5 | 120.00 |
C8—N1—H1 | 125 (3) | C6—C5—H5 | 120.00 |
C14—N2—H2A | 117.00 | C1—C6—H6 | 120.00 |
S1—N2—H2A | 117.00 | C5—C6—H6 | 120.00 |
C2—C1—C7 | 119.6 (3) | N1—C7—H7 | 118.00 |
C2—C1—C6 | 119.9 (4) | C1—C7—H7 | 118.00 |
C6—C1—C7 | 120.4 (3) | C8—C9—H9 | 120.00 |
C1—C2—C3 | 118.7 (3) | C10—C9—H9 | 120.00 |
O1—C2—C1 | 122.0 (3) | C9—C10—H10 | 120.00 |
O1—C2—C3 | 119.4 (3) | C11—C10—H10 | 120.00 |
C2—C3—C4 | 119.2 (4) | C11—C12—H12 | 120.00 |
O2—C3—C2 | 121.7 (3) | C13—C12—H12 | 120.00 |
O2—C3—C4 | 119.1 (4) | C8—C13—H13 | 120.00 |
C3—C4—C5 | 121.8 (4) | C12—C13—H13 | 120.00 |
C4—C5—C6 | 120.5 (4) | C15—C16—H16 | 121.00 |
C1—C6—C5 | 119.8 (4) | C17—C16—H16 | 121.00 |
N1—C7—C1 | 123.4 (4) | C17—C18—H18A | 109.00 |
N1—C8—C9 | 121.5 (3) | C17—C18—H18B | 109.00 |
C9—C8—C13 | 120.7 (4) | C17—C18—H18C | 109.00 |
N1—C8—C13 | 117.8 (3) | H18A—C18—H18B | 109.00 |
C8—C9—C10 | 119.8 (3) | H18A—C18—H18C | 109.00 |
C9—C10—C11 | 120.1 (3) | H18B—C18—H18C | 109.00 |
S1—C11—C10 | 120.5 (3) | C15—C19—H19A | 109.00 |
S1—C11—C12 | 119.1 (3) | C15—C19—H19B | 109.00 |
C10—C11—C12 | 120.3 (3) | C15—C19—H19C | 109.00 |
C11—C12—C13 | 119.4 (3) | H19A—C19—H19B | 109.00 |
C8—C13—C12 | 119.8 (4) | H19A—C19—H19C | 109.00 |
N2—C14—N4 | 117.3 (3) | H19B—C19—H19C | 109.00 |
O3—S1—N2—C14 | −173.5 (3) | C2—C1—C6—C5 | −1.6 (6) |
O4—S1—N2—C14 | 57.7 (3) | C7—C1—C6—C5 | 177.9 (4) |
C11—S1—N2—C14 | −59.3 (3) | C2—C1—C7—N1 | 1.0 (6) |
O3—S1—C11—C10 | −149.8 (3) | C6—C1—C7—N1 | −178.5 (4) |
O3—S1—C11—C12 | 34.1 (3) | O1—C2—C3—O2 | 1.6 (6) |
O4—S1—C11—C10 | −18.0 (3) | O1—C2—C3—C4 | −179.2 (4) |
O4—S1—C11—C12 | 165.9 (3) | C1—C2—C3—O2 | −178.1 (4) |
N2—S1—C11—C10 | 100.5 (3) | C1—C2—C3—C4 | 1.1 (6) |
N2—S1—C11—C12 | −75.6 (3) | O2—C3—C4—C5 | 177.8 (4) |
C8—N1—C7—C1 | 180.0 (4) | C2—C3—C4—C5 | −1.5 (7) |
C7—N1—C8—C9 | 34.0 (6) | C3—C4—C5—C6 | 0.3 (7) |
C7—N1—C8—C13 | −146.0 (4) | C4—C5—C6—C1 | 1.2 (7) |
S1—N2—C14—N3 | 170.9 (3) | N1—C8—C9—C10 | −178.8 (4) |
S1—N2—C14—N4 | −8.9 (5) | C13—C8—C9—C10 | 1.1 (6) |
C15—N3—C14—N2 | 177.7 (3) | N1—C8—C13—C12 | 179.3 (4) |
C15—N3—C14—N4 | −2.5 (6) | C9—C8—C13—C12 | −0.7 (6) |
C14—N3—C15—C16 | 0.3 (5) | C8—C9—C10—C11 | −0.7 (6) |
C14—N3—C15—C19 | 179.4 (3) | C9—C10—C11—S1 | −176.4 (3) |
C17—N4—C14—N2 | −178.0 (3) | C9—C10—C11—C12 | −0.3 (5) |
C17—N4—C14—N3 | 2.2 (6) | S1—C11—C12—C13 | 176.9 (3) |
C14—N4—C17—C16 | 0.1 (5) | C10—C11—C12—C13 | 0.8 (5) |
C14—N4—C17—C18 | −178.5 (3) | C11—C12—C13—C8 | −0.3 (6) |
C6—C1—C2—O1 | −179.3 (4) | N3—C15—C16—C17 | 1.7 (6) |
C6—C1—C2—C3 | 0.4 (6) | C19—C15—C16—C17 | −177.3 (4) |
C7—C1—C2—O1 | 1.2 (6) | C15—C16—C17—N4 | −1.9 (6) |
C7—C1—C2—C3 | −179.1 (4) | C15—C16—C17—C18 | 176.6 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1 | 0.78 (4) | 1.88 (4) | 2.569 (5) | 148 (4) |
O2—H2···O1 | 0.82 | 2.34 | 2.768 (5) | 113 |
O2—H2···N3i | 0.82 | 2.16 | 2.862 (5) | 144 |
N2—H2A···O1ii | 0.86 | 1.94 | 2.790 (4) | 172 |
C18—H18A···O4iii | 0.96 | 2.52 | 3.469 (5) | 171 |
Symmetry codes: (i) −x+1/2, −y+1/2, z−1/2; (ii) −x+1/2, −y+1/2, z+1/2; (iii) x, −y, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C19H18N4O4S |
Mr | 398.43 |
Crystal system, space group | Orthorhombic, Pbcn |
Temperature (K) | 296 |
a, b, c (Å) | 24.7506 (12), 12.1689 (6), 12.8408 (5) |
V (Å3) | 3867.5 (3) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.20 |
Crystal size (mm) | 0.34 × 0.28 × 0.15 |
Data collection | |
Diffractometer | Bruker Kappa APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.935, 0.971 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16627, 3796, 1778 |
Rint | 0.069 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.054, 0.151, 1.01 |
No. of reflections | 3796 |
No. of parameters | 259 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.21, −0.28 |
Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1 | 0.78 (4) | 1.88 (4) | 2.569 (5) | 148 (4) |
O2—H2···O1 | 0.82 | 2.34 | 2.768 (5) | 113 |
O2—H2···N3i | 0.82 | 2.16 | 2.862 (5) | 144 |
N2—H2A···O1ii | 0.86 | 1.94 | 2.790 (4) | 172 |
C18—H18A···O4iii | 0.96 | 2.52 | 3.469 (5) | 171 |
Symmetry codes: (i) −x+1/2, −y+1/2, z−1/2; (ii) −x+1/2, −y+1/2, z+1/2; (iii) x, −y, z−1/2. |
Acknowledgements
The authors acknowledge the provision of funds for the purchase of the diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan.
References
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chohan, Z. H., Tahir, M. N., Shad, H. A. & Khan, I. U. (2008). Acta Cryst. E64, o648. Web of Science CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Shad, H. A., Tahir, M. N. & Chohan, Z. H. (2009). Acta Cryst. E65, o98–o99. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tahir, M. N., Khan, A. H., Iqbal, M. S., Munir, C. & Aziz, T. (2012). Acta Cryst. E68, o2125. CSD CrossRef IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
We have reported the crystal structure of 4-{[(E)-(2,3-dihydroxyphenyl) methylidene]amino}-N-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide (Tahir et al., 2012) and the title compound (I), (Fig. 1) has also been synthesized for the biological studies and forming different metal complexes.
The crystal structures of 4-(5-chloro-2-hydroxybenzylideneamino)-N- (4,6-dimethylpyrimidin-2-yl)benzenesulfonamide (Chohan et al., 2008) and 4-[(5-bromo-2-hydroxybenzylidene)amino]-N-(4,6-dimethylpyrimidin- 2-yl)benzenesulfonamide–4-bromo-2-[(E)-({4-[(4,6-dimethylpyrimidin-2-yl) sulfamoyl]phenyl}iminio)methyl]phenolate (Shad et al., 2009) have been published which are related to the title compound.
In (I) the parts of 2,3-dihydroxybenzaldehyde A (C1—C7/O1/O2), annilinic group B (C8—C13/N1) and 4,6-dimethylpyrimidin-2-amine C (C14—C19/N2/N3/N4) are planar with r.m.s. deviation of 0.0105, 0.0070 and 0.0216 Å, respectively. The dihedral angle between A/B, A/C and B/C is 35.51 (11)°, 76.99 (6)° and 88.92 (6)°, respectively. The sulfonyl group D (O3/S1/O4) is of course planar. The dihedral angle between A/D, B/D and C/D is 62.20 (13)°, 47.66 (17)° and 50.34 (15)°, respectively. In (I), S(5) and S(6) ring motif (Bernstein et al., 1995) are present due to H-bondings of O—H···O and N—H···O types, respectively (Table 1, Fig. 1). The molecules are interlinked from end to end due to H-bondings of N—H···O and O—H···O types (Table 1, Fig. 2). Due to these bondings R23(6) loops are also formed. The molecules are interlinked in the form of polymeric chains along the c-axis. The polymeric chains are also interlinked due to C–H···O bondings (Table 1, Fig. 2), Where CH is of methyl group and O-atom is of sulfonyl group. There exist π–π interaction between Cg1···Cg1i [i = 1 - x, y, 1/2 - z] at a distance of 3.446 (2) Å, where Cg1 is the centroid of pyrimidin ring (C14—C17/N3/N4).